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MedKoo Cat#: 592984 | Name: Asimadoline
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Asimadoline is a potent κ-opioid receptor (KOR) agonist and spasmolytic. In vivo, asimadoline reduces joint damage in a rat model of arthritis induced by complete Freund's adjuvant (CFA). Asimadoline also reduces the abdominal withdrawal reflex in a model of visceral pain induced by colonic distension in wild-type, but not KOR-/-, mice.

Chemical Structure

Asimadoline
Asimadoline
CAS#153205-46-0 (free base)

Theoretical Analysis

MedKoo Cat#: 592984

Name: Asimadoline

CAS#: 153205-46-0 (free base)

Chemical Formula: C27H30N2O2

Exact Mass: 414.2307

Molecular Weight: 414.55

Elemental Analysis: C, 78.23; H, 7.29; N, 6.76; O, 7.72

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
25mg USD 1,050.00 2 Weeks
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Related CAS #
153205-46-0 (free base) 185951-07-9 (HCl)
Synonym
Asimadoline; EMD 61753; EMD61753; EMD-61753
IUPAC/Chemical Name
Benzeneacetamide, N-((1S)-2-((3S)-3-hydroxy-1-pyrrolidinyl)-1-phenylethyl)-N-methyl-alpha-phenyl-
InChi Key
JHLHNYVMZCADTC-LOSJGSFVSA-N
InChi Code
InChI=1S/C27H30N2O2/c1-28(25(21-11-5-2-6-12-21)20-29-18-17-24(30)19-29)27(31)26(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,24-26,30H,17-20H2,1H3/t24-,25+/m0/s1
SMILES Code
O=C(N([C@@H](C1=CC=CC=C1)CN2C[C@@H](O)CC2)C)C(C3=CC=CC=C3)C4=CC=CC=C4
Appearance
A crystalline solid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 414.55 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Mangel AW, Williams VS. Asimadoline in the treatment of irritable bowel syndrome. Expert Opin Investig Drugs. 2010 Oct;19(10):1257-64. doi: 10.1517/13543784.2010.515209. PMID: 20809870. 2: Camilleri M. Novel pharmacology: asimadoline, a kappa-opioid agonist, and visceral sensation. Neurogastroenterol Motil. 2008 Sep;20(9):971-9. doi: 10.1111/j.1365-2982.2008.01183.x. PMID: 18715494; PMCID: PMC2698012. 3: Mangel AW, Hicks GA. Asimadoline and its potential for the treatment of diarrhea-predominant irritable bowel syndrome: a review. Clin Exp Gastroenterol. 2012;5:1-10. doi: 10.2147/CEG.S23274. Epub 2012 Jan 12. PMID: 22346361; PMCID: PMC3278196. 4: Talley NJ, Choung RS, Camilleri M, Dierkhising RA, Zinsmeister AR. Asimadoline, a kappa-opioid agonist, and satiation in functional dyspepsia. Aliment Pharmacol Ther. 2008 Jun 1;27(11):1122-31. doi: 10.1111/j.1365-2036.2008.03676.x. Epub 2008 Mar 7. PMID: 18331462; PMCID: PMC3935285. 5: Mangel AW, Bornstein JD, Hamm LR, Buda J, Wang J, Irish W, Urso D. Clinical trial: asimadoline in the treatment of patients with irritable bowel syndrome. Aliment Pharmacol Ther. 2008 Jul;28(2):239-49. doi: 10.1111/j.1365-2036.2008.03730.x. Epub 2008 May 7. PMID: 18466359. 6: Marsella R, Ahrens K, Wilkes R, Soeberdt M, Abels C. Topical κ-opioid receptor agonist asimadoline improves dermatitis in a canine model of atopic dermatitis. Exp Dermatol. 2022 Apr;31(4):628-632. doi: 10.1111/exd.14507. Epub 2021 Dec 5. PMID: 34839557. 7: Schreiber R, Bartoszyk GD, Kunzelmann K. The kappa-opioid receptor agonist asimadoline inhibits epithelial transport in mouse trachea and colon. Eur J Pharmacol. 2004 Oct 25;503(1-3):185-90. doi: 10.1016/j.ejphar.2004.09.038. PMID: 15496313. 8: Delgado-Aros S, Chial HJ, Cremonini F, Ferber I, McKinzie S, Burton DD, Camilleri M. Effects of asimadoline, a kappa-opioid agonist, on satiation and postprandial symptoms in health. Aliment Pharmacol Ther. 2003 Sep 1;18(5):507-14. doi: 10.1046/j.1365-2036.2003.01670.x. PMID: 12950423. 9: Delgado-Aros S, Chial HJ, Camilleri M, Szarka LA, Weber FT, Jacob J, Ferber I, McKinzie S, Burton DD, Zinsmeister AR. Effects of a kappa-opioid agonist, asimadoline, on satiation and GI motor and sensory functions in humans. Am J Physiol Gastrointest Liver Physiol. 2003 Apr;284(4):G558-66. doi: 10.1152/ajpgi.00360.2002. PMID: 12631557. 10: Binder W, Walker JS. Effect of the peripherally selective kappa-opioid agonist, asimadoline, on adjuvant arthritis. Br J Pharmacol. 1998 Jun;124(4):647-54. doi: 10.1038/sj.bjp.0701874. PMID: 9690855; PMCID: PMC1565434. 11: Szarka LA, Camilleri M, Burton D, Fox JC, McKinzie S, Stanislav T, Simonson J, Sullivan N, Zinsmeister AR. Efficacy of on-demand asimadoline, a peripheral kappa-opioid agonist, in females with irritable bowel syndrome. Clin Gastroenterol Hepatol. 2007 Nov;5(11):1268-75. doi: 10.1016/j.cgh.2007.07.011. Epub 2007 Sep 27. PMID: 17900994; PMCID: PMC2128734. 12: Kramer HJ, Uhl W, Ladstetter B, Bäcker A. Influence of asimadoline, a new kappa-opioid receptor agonist, on tubular water absorption and vasopressin secretion in man. Br J Clin Pharmacol. 2000 Sep;50(3):227-35. doi: 10.1046/j.1365-2125.2000.00256.x. PMID: 10971307; PMCID: PMC2014989. 13: Delvaux M, Beck A, Jacob J, Bouzamondo H, Weber FT, Frexinos J. Effect of asimadoline, a kappa opioid agonist, on pain induced by colonic distension in patients with irritable bowel syndrome. Aliment Pharmacol Ther. 2004 Jul 15;20(2):237-46. doi: 10.1111/j.1365-2036.2004.01922.x. PMID: 15233705. 14: Jolivalt CG, Jiang Y, Freshwater JD, Bartoszyk GD, Calcutt NA. Dynorphin A, kappa opioid receptors and the antinociceptive efficacy of asimadoline in streptozotocin-induced diabetic rats. Diabetologia. 2006 Nov;49(11):2775-85. doi: 10.1007/s00125-006-0397-y. Epub 2006 Aug 19. PMID: 16924480. 15: Bush KA, Kirkham BW, Walker JS. The kappa-opioid agonist, asimadoline, alters cytokine gene expression in adjuvant arthritis. Rheumatology (Oxford). 2001 Sep;40(9):1013-21. doi: 10.1093/rheumatology/40.9.1013. PMID: 11561112. 16: Walker JS, Scott C, Bush KA, Kirkham BW. Effects of the peripherally selective kappa-opioid asimadoline, on substance P and CGRP mRNA expression in chronic arthritis of the rat. Neuropeptides. 2000 Jun-Aug;34(3-4):193-202. doi: 10.1054/npep.2000.0813. PMID: 11021980. 17: Caram-Salas NL, Reyes-García G, Bartoszyk GD, Araiza-Saldaña CI, Ambriz- Tututi M, Rocha-González HI, Arreola-Espino R, Cruz SL, Granados-Soto V. Subcutaneous, intrathecal and periaqueductal grey administration of asimadoline and ICI-204448 reduces tactile allodynia in the rat. Eur J Pharmacol. 2007 Nov 14;573(1-3):75-83. doi: 10.1016/j.ejphar.2007.06.034. Epub 2007 Jun 29. PMID: 17643411. 18: Jonker JW, Wagenaar E, van Deemter L, Gottschlich R, Bender HM, Dasenbrock J, Schinkel AH. Role of blood-brain barrier P-glycoprotein in limiting brain accumulation and sedative side-effects of asimadoline, a peripherally acting analgaesic drug. Br J Pharmacol. 1999 May;127(1):43-50. doi: 10.1038/sj.bjp.0702497. PMID: 10369454; PMCID: PMC1565984. 19: Walker J, Catheline G, Guilbaud G, Kayser V. Lack of cross-tolerance between the antinociceptive effects of systemic morphine and asimadoline, a peripherally-selective kappa-opioid agonist, in CCI-neuropathic rats. Pain. 1999 Dec;83(3):509-516. doi: 10.1016/S0304-3959(99)00158-X. PMID: 10568859. 20: Binder W, Scott C, Walker JS. Involvement of substance P in the anti- inflammatory effects of the peripherally selective kappa-opioid asimadoline and the NK1 antagonist GR205171. Eur J Neurosci. 1999 Jun;11(6):2065-72. doi: 10.1046/j.1460-9568.1999.00625.x. PMID: 10336675.

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